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Synthesis 1990; 1990(12): 1167-1169
DOI: 10.1055/s-1990-27125
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Synthesis of (E)-4-Oxo-5-hexenals and Their Acetal Derivatives

Shuji Kanemasa* , Tatsuya Otsuka, Kenji Doi, Otohiko Tsuge, Eiji Wada
  • *Institute of Advanced Material Study, Kyushu University, Kasugakoen, Kasuga 816, Japan
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Publication Date:
02 May 2002 (online)

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An effective synthesis of (E)-4-oxo-5-hexenals 6 and the acetals 5 starting from ethyl 2-alkoxy-1-cyclopropanecarboxylates 1a-d is presented. The acid-induced ring opening of the cyclopropanecarboxylates 1a, b, followed by phosphorylmethylation or the phosphorylmethylation of the ester 1c followed by ring opening leads to the 5-acetal of 2,5-dioxopentylphosphonate 4. The Horner-Emmons olefination of 4 with various aldehydes produces the title compounds.

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